L-Homotyrosine

Base Information

• Chemical Name: L-Homotyrosine
• CAS No.: 221243-01-2
• Molecular Formula: C10H13 N O3
• Molecular Weight: 195.218
• UNII: 15X6A9Y291
• DSSTox Substance ID: DTXSID40569328
• Metabolomics Workbench ID: 78639
• Nikkaji Number: J1.321.572C
• Wikidata: Q27155634
• Mol file: 221243-01-2.mol

Synonyms:(+)-homotyrosine;(+-)-homotyrosine;(S)-alpha-amino-4-hydroxybenzenebutanoic acid;alpha-amino-4-hydroxybenzenebutanoic acid;homotyrosine

Chemical Property of L-Homotyrosine

Chemical Property:

• Melting Point: 217-220 °C
• Boiling Point: 397°Cat760mmHg
• PKA: 2.30±0.10(Predicted)
• Flash Point: 193.9°C
• PSA: 83.55000
• Density: 1.281g/cm³
• LogP: 2.39510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-2-Amino-4-(4-hydroxyphenyl)butanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC(C(=O)O)N)O
• Isomeric SMILES: C1=CC(=CC=C1CC[C@@H](C(=O)O)N)O

Technology Process of L-Homotyrosine

There total 22 articles about L-Homotyrosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

C13H14F3NO4 (1263096-03-2) → (S)-homotyrosine (221243-01-2,185062-84-4)

Guidance literature:

With hydrogenchloride; water; at 80 ℃; for 6h;

DOI:10.1016/j.tet.2010.11.047

Reference yield: 73.0%

O-methyl-L-homotyrosine (82311-00-0,82310-97-2) → (S)-homotyrosine (221243-01-2,185062-84-4)

Guidance literature:

With hydrogen iodide; for 15h; Reflux;

DOI:10.1007/s00726-016-2263-7

Reference yield: 45.0%

Acetic acid 4-((3aS,7S)-4-oxo-7-phenyl-hexahydro-isoxazolo[3,2-c][1,4]oxazin-2-yl)-phenyl ester (368875-94-9) → (S)-homotyrosine (221243-01-2,185062-84-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In 1,4-dioxane; trifluoroacetic acid; under 3102.89 Torr;

DOI:10.1016/S0040-4039(01)00821-8

upstream raw materials:

Acetic acid 4-((3aS,7S)-4-oxo-7-phenyl-hexahydro-isoxazolo[3,2-c][1,4]oxazin-2-yl)-phenyl ester

2-Chloroanisole

(S)-4-(3-Chloro-4-methoxy-phenyl)-2-(3-methyl-ureido)-4-oxo-butyric acid

p-acetoxystyrene

Downstream raw materials:

4-(4-benzyloxycarbonylamino-phenyl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

L-N^α-(tert-butoxycarbonyl)-4-(N-benzyloxycarbonylamino)-homophenylalanine

4-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propyl)-benzoic acid

Boc-hTyr(CH₂OH)OMe

Refernces

• 1、 -. "Method for Preparing Unnatural Amino Acids". Paragraph 0172; 0173; 0203; 0204. . Retrieved 2017/01/09.
• 2、 Okumura, Hilary S.,Philmus, Benjamin,Portmann, Cyril,Hemscheidt, Thomas K.. "Homotyrosine-containing cyanopeptolins 880 and 960 and anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8". experimental part. p. 172 - 176. Retrieved 2009/06/27.